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Issue 85, 2017
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Aza-capped cyclodextrins for intra-cavity metal complexation

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Aza-capped, methylated cyclodextrins (CDs) were obtained in high yields by reacting the soft nitrogen nucleophile 2-nitrobenzenesulfonamide with either A,B-dimesylated CDs in basic media or their diol analogues under Mitsunobu reaction conditions followed by deprotection with thiophenol. A methyl pyridine substituent was grafted on the N atom of these secondary amines. When built on an α-CD scaffold, the resulting tertiary amine no longer undergoes nitrogen inversion at room temperature and behaves as a confining ligand, opening the way to intra-cavity metal complexation and promoting the formation of supramolecular helices.

Graphical abstract: Aza-capped cyclodextrins for intra-cavity metal complexation

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Article information

16 Aug 2017
29 Sep 2017
First published
12 Oct 2017

Chem. Commun., 2017,53, 11717-11720
Article type

Aza-capped cyclodextrins for intra-cavity metal complexation

D. Sechet, Z. Kaya, T.-A. Phan, M. Jouffroy, E. Bentouhami, D. Armspach, D. Matt and L. Toupet, Chem. Commun., 2017, 53, 11717
DOI: 10.1039/C7CC06434A

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